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Aliphatic Synthetic Routes

OCR A-level Organic ChemistryOrganic SynthesisLesson 7 of 9

An aliphatic synthetic route converts one non-aromatic compound into another in one or more steps. You need to recall the reagents and conditions linking the functional groups in the specification:

• alkene → alcohol: steam, H3PO4 catalyst
• alkene → haloalkane: hydrogen halide (e.g. HBr) at room temperature
• alcohol → alkene: acid catalyst (conc. H3PO4 or H2SO4), heat
• alcohol → haloalkane: NaBr and conc. H2SO4 (forms HBr)
• haloalkane → alcohol: NaOH(aq), heat under reflux
• haloalkane → nitrile: KCN in ethanol (adds one carbon)

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Key terms in this lesson

nitrile
A compound containing the -C≡N functional group, often made by reacting a haloalkane with cyanide ions.
hydroxynitrile
A compound formed by nucleophilic addition of hydrogen cyanide to an aldehyde or ketone, containing both a hydroxyl and a nitrile group.

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